Have always used a combination of CityStrides and On the Go Map, and recently started using SportsTracker, an app @christophe.cr92 mentioned in this thread about tracking runs live.
I previously enjoyed printing out the map and running with it, or actually writing out the directions and turns and then trying to figure out what I meant on the run! 
makes for mentally engaging work, but sucks when I can’t figure it out myself!
@dallas.devries, wanted to point out that there are some other very similar threads, including:
- Add a Route Suggestion Feature: the OG route-building post by @JamesChevalier himself, some relevant comments there where people share
- Chinese Postman Problem: a specific technical discussion about the route building issue and the developmental considerations of adding the feature to CS